Treatment of textile and other materials



Patented May 8, 1934 TREATMENT OF TEXTILE AND OTHER MATERIALS George Holland Ellis,

Ernest William Kirk, Spondon,

Henry Charles Olpin, and.

near Derby,

England, assignors to Celanese Corporation of America, a corporation of Delaware No Drawing. Application March 19, 1931,

Serial No. 523,941. In Great Britain March 21, 1930 21 Claims.

This invention relates to the treatment of textile yarns, threads, fabrics and other materials and especially materials made of or containing cellulose acetate or other organic substitution derivatives of cellulose.

We have found that acid amides, especially those of the higher fatty acids, constitute valuable materials for the treatment of or incorporation in textile and other materials, especially materials made of or containing cellulose acetate or other cellulose esters or ethers. Thus acid amides of a basic character, e. g. mono-oleyl or other monoacidyl derivatives of aliphatic diamines applied to cellulose ester or ether textile materials effect a marked improvement in the fastness of colourations produced thereon by means of certain colouring matters, particularly amino-anthraquinones. The improvement is particularly noticeable in respect to fastness to light or the 20 combined agencies of light and acid (e. g. acid fumes).

Again, by means of the aforesaid basic acid amide derivatives and also by means of other acid amides, textile filaments, yarns, or threads may be rendered more amenable to winding, twisting, knitting and other textile operations, while fabrics may be caused to acquire an improved feel or handle. The acid amide derivatives may therefore be employed in place of the oils, fats, etc., commonly used in the lubrication, softening, dressing, etc., of textile materials.

By utilizing acid amide derivatives it thus is possible to effect the lubrication, softening, etc., of textile materials and simultaneously to increase the fastness of any colourations applied thereto. Further, the entire manufacture and treatment of textile materials, from the filaments or yarn stage up to the production of finished fabrics, may be effected without the use of substances, such as fats or oils, liable to develop acidity which may be prejudicial to any colourations applied to the materials.

Broadly, therefore our invention comprises the incorporation in textile filaments, threads, yarns, fabrics and other materials of carboxylic acid amides and especially carboxylic acid amides substituted in the amide group by aliphatic residues whether simple hydrocarbon residues or substi- 50 tuted hydrocarbon residues.

As examples of compounds suitable for incorporating in textile materials in accordance with the invention may be mentioned the amides, alkylamides and substituted alkylamides of acids containing more than four carbon atoms, e. g.

more than eight carbon atoms, and especially of the higher fatty acids. For instance, there may be used the amides, alkylamides and substituted alkylamides of lauric, myristic, stearic, palmitic and oleic acids or of other saturated or unsaturatedfatty acids'or mixtures containing these acids; for example there may be used oleic acid amide, oleic acid methylamide, undecylenic acid diethylamide. As examples of substituted alkylamides may be mentioned oxyethylor other oxylkylamides of oleic and other higher fatty acids, aminoalkylamides of these acids 1. e. acidylated aliphatic dior poly-amines. The acidylated diamine compounds may have the general formula RR2N-R1NR3R4, wherein R is an aliphatic or aromatic acidyl group, R1 is an aliphatic residue and R2, R3 and R4 are hydrogen or aliphatic groups. Any of the groups R, R1, R2, R3 and R4 may contain further substituents and the residue R1 may consist of a chain composed entirely of carbon atoms or composed in part of carbon atoms and in part of other atoms, for example nitrogen or sulphur. The residuesRa and R4 are not necessarily independent substituents but may, in conjunction with the nitrogen atom, form a cyclic radicle, for example the piperidyl radicle. All these acid amides and substituted acid amides are hereinafter referred to as acid amide compounds.

For lubricating purposes it is found in general that the acid amide compounds derived from the higher fatty acids are especially suitable, particularly the alylamides or substituted alklamides, the application of which is facilitated by their low melting points. For instance, textile materials may be very satisfactorily lubricated by means of oleic acid ethylamide or by means of oleyl diethyl ethylene diamine.

Where it is desired to impart to colourations applied to the materials a high degree of resistance to fading in the presence of acid and light it is preferred to use for incorporation in the materials an acid amide compound of a relatively strongly basic character, for example one of the mono-acidyl diamine' derivatives referred to above. The oleyl diethyl-ethylene-diamine or oleyl w-amino N-ethyl-piperidine or oleyl-[31% diamino-diethylamine may be employed with great success for this purpose. It is an advantage in such case to select an acid amide compound having a substantive affinity for the material in order that it may be incapable of removal by washing or like treatments.

If desired other substances capable of improving the fastness of colourations on the materials mentioned in United States application S. No.

450,308 filed 6th May, 1930 (the alkylated aminodiaryl bases mentioned in United States application S. No. 449,082 filed 1st May, 1930, and the aralkylated bases mentioned in British application No. 15008/30 filed 15th May, 1930.

The proportion of acid amide compound employed-may vary within wide limits according to the effect required. The application of from 0.1 to 2%, based on the weight of the material, has been found to give satisfactory results in preventing fading, under acid conditions, of colourations on cellulose ester and ether materials. As a finish to textile fabrics, 1 to 2% may be employed.

The incorporation of the acid amide compounds in the materials may be accomplished in any desired manner. In the case of artificial filaments for instance, the compounds may be incorporated in the solutions from which the filaments are to'be manufactured. In general, however, it is more convenient to apply the compounds to previously manufactured yarns, threads, fabrics, etc. The compounds may for instance be applied in the concentrated state in the case of liquids, or they may be applied in solution in suitable solvents or in the form of aqueous emulsions or dispersions produced with the aid of any convenient dispersing agents. Solutions may for instance be prepared with the aid of volatile alcohols, esters,

hydrocarbons, or chlorinated hydrocarbons. Some of the amide compounds, especially oleyl ethylene diamines and other strongly basic derivatives may be dissolved in aqueous acids and applied in this form. From such acid solutions the basic compound is substantively absorbed by some materials, especially those made of or containing cellulose esters or ethers.

The use of emulsifying and dispersing agents of acid character is preferably avoided in the preparation of dispersions or emulsions of acid amide compounds intended to afford colourations on the materials treated the maximum possible degree of protection against fading. The acid amide compounds may for instance be emulsified by dissolving in solvents and pouring into a precipitating medium containing a protective colloid, for instance an aqueous solution of gelatin, casein or the like. Mechanical means, e. g. grinding or milling with water, may also usefully be employed in the preparation of emulsions or dispersions, with or without the aid of dispersing agents or protective colloids.

Emulsions and dispersions of the acid amide compounds may be directly prepared of a strength suitable for application to the textile materials. If desired, however, the acid amide compounds may first be brought into the form of solid, powdered, paste, liquid or other more or less concentrated preparations capable of yielding, by dilution with water, soap solution. or the like, treatment baths containing the acid amide compounds in suitably dispersed form. These preparations may be prepared for instance by evaporating or otherwise removing water from less concentrated preparations or by simple grinding or mixing of the acid amide compounds with dispersing agents and/or protective colloids with or without water. In the case of strongly basic compounds such as oleyl diethyl ethylene diamine, their salts, for example the hydrochlorides, may be ground or mixed with dispersing agents and/ or protective colloids whereby preparations may be obtained which yield very satisfactory dispersipns on dissolving in water and liberating the free basic compound by addition of alkali.

If desired the preparations may also contain dyestuffs, for example insoluble or difilcultly soluble colouring matters of the amino anthraquinone or other series, such as are frequently utillzed for the colouration of celulose ester materials. In this manner preparations may be obtained capable of yielding dye-baths from which cellulose acetate or other cellulose esters or cellulose ethers may be dyed in shades very resistant to fading in the presence of acid and light.

The application to-the materials oi. the acid amide compounds or solutions, emulsions or dispersions containing them, may be effected in any convenient manner. Emulsions, dispersions, or solutions may for instance be applied to textile materials by dyeing or padding, and either before, after, or simultaneously with a colouration of the materials. Threads and yarns may be similarly treated, for instance in the form of hanks or on bobbins. Threads, yarns, etc. may also be passed through baths containing the compounds or solutions or emulsions of the same, or be passed over rollers, wicks, or other devices supplied with the compounds or solutions, emulsions, or dispersions thereof. Conveniently, application by this method may be effected simultaneously with other textile operations such as winding or twisting, or, in the case of artificial filaments, with the manufacture of the same. Thus, filaments of cellulose acetate produced by a dry-spinning process may be led directly from the spinning cell over a .wick or other device supplied with a higher fatty acid amide compound,

whereby they may be lubricated satisfactorily prior to winding or twisting and winding; For application to travelling filaments, threads, yarns, etc., compounds which are liquid at ordinary temperatures are the most convenient as .they may be directly applied in the absence of volatile solvents or other admixtures.

The invention-is applicable to the treatment of textile or cellulose or cellulose derivative materials of all kinds,'and is especially applicable, to the treatment of materials made of or containing cellulose acetate and other organic derivatives of cellulose, for example materials made of or containing cellulose formate, propionate, or butyrate or cellulose ethers, e. g. methyl, ethyl or benzyl cellulose. Mixed materials, for example materials comprising one of the aforesaid organic derivatives of cellulose in admixture with cotton, wool, or silk may likewise be treated in accordance with the invention.

The invention is illustrated but not limited by the following examples:

Example 1 of unsymmetrical oleyl-ethylenediamin'e, previously dispersed with three times its weight of 50% Turkey red oil. Dyeing is carried on at a maximum temperature of 75-80 C. for 1-l hours, or until the desired depth of shade has been achieved, when the goods are removed and washed or otherwise aftertreated as desired.

The above mentioned ethylenediamine derivative may be prepared by heating oleic acid with unsymmetrical dimethylethylenediamine in an autoclave.

Example 2 A fabric of cellulose acetate yarn, which has been dyed with 1: 4-di-(monoethanolamino) anthraquinone in a shade of blue, is entered into a bath containing 10 cos. per litre of unsymmetrical palmityl-diethyl-ethylenediamine, which has been dispersed with Turkey red oil, and gently worked until thoroughly impregnated, when it is hydro-extracted without rinsing, and dried and finished as requisite.

The above mentioned protective compound may be made by treating palmit'yl chloride with unsymmetrical diethylethylene diamine.

Example 3 A cellulose acetate fabric is dyed in the manner described in Example 1, but with oleylamide replacing in equivalent quantity the ethylenediamine derivative mentioned in that example.

Example 4 Cellulose acetate yarn is lubricated immediately following the actual spinning operation and prior to winding, by means of oleylmethylamide, used in full strength without admixture or dilution. To effect application the yarn may be passed over pads or wicks supplied with the liquid oleylmethylamide. The yarn is thus rendered suitable for knitting or other textile operation.

What we claim and desire to secure by Letters Patent is:

1. Process for improving the fastness to light of colorations produced by dyes on materials comprising an organic derivative of cellulose, which comprises incorporating in the materials a compound selected from the group consisting of the amides and substituted amides of higher fatty carboxylic acids, and retaining said compound in the materials.

2. Process for improving the fastness to light of colorations produced by dyes on materials comprising cellulose acetate, which comprises incorporating in the materials a compound selected from the group consisting of the amides and substituted amides of the organic carboxylic acids containing more than four carbon atoms, and retaining said compound in the materials.

3. Process for improving the fastness to light of colorations produced by dyes on materials comprising an organic derivative of cellulose, which comprises incorporating in the materials a compound selected from the group consisting of the amides and substituted amides of organic carboxylic acids containing more than four carbon atoms, and retaining said compound in the materials.

4. Process for improving the fastness to light of colorations produced by dyes on materials comprising an organic derivative of cellulose, which comprises incorporating in the materials a compound selected from the group consisting of the alkylamides, substituted alkylamides, amides of oleic, palmitic, lauric, myristic and stearic acids, and retaining said compound in the materials.

5. Process for improving the fastness to light of colorations produced by dyes on materials comprising cellulose acetate, which comprises incorporating in the materialsa compound selected from the group consisting of the alkylamides, substituted alkylamides, amides of oleic, palmitic,

lauric, myristic and stearic acids, and retaining said compound in the materials.

6. Process for increasing the fastness of colora tions produced with the aid of anthraquinone dyestuffs on materialscomprising an organic derivative of cellulose, which comprises incorporating in the materials a compound selected from the group consisting of the amides and substituted amides of an organic carboxylic. acid containing more-than four carbon atoms and retaining said compound in the materials.

7 Process for increasing the fastness of colorations produced with the aid of anthraquinone dyestufi's on materials comprising cellulose acetate, which comprises incorporating in the mate rials a compound selected from the group consisting of the amides and. substituted amides of an organic carboxylic acid containing more than four carbon atoms and retaining said compound in the materials.

8. Process for improving the fastness to light of colorations produced by dyes on materials comprising incorporating in the materials a compound having the general formula RR2NR1 NR3R4 wherein R, is an aliphatic acidyl'group containing more than four carbon atoms R1 is an aliphatic residue and RzRs and R4 are hydrogen or aliphatic groups and retaining said compound in the materials.

9. Process for improving the fastness of colorations produced with the aid of anthraquinone dyestuffs on materials comprising an organic derivative of cellulose, which comprises incorporating in the materials a compound selected from the group consisting of the amides, alkylamides and substituted alkylamides of oleic, palmitic, lauric, myristic and stearic acids, and retaining said compound in the materials.

10. Process for improving the fastness of colorations produced with the aid of anthraquinone dyestuffs on materials comprising cellulose acetate, which comprises incorporating in the materials a compound selected from the group consisting of the amides, alkylamides and substituted alkylamides of oleic, palmitic, lauric, myristic and stearic acids, and retaining said compound in the materials.

11. Process for increasing the fastness to light of colorations produced by dyes on materials comprising an organic derivative of cellulose, which comprises incorporating in the materials a compound selected from the group consisting of the higher fatty acidyl derivatives of ethylene diamine and the substituted ethylene diamines and retaining said compound in the materials.

12. Process for increasing the fastness to light of colorations produced by dyes on materials comprising cellulose acetate, which comprises incorporating in the materials a compound selected from the group consisting of the oleyl, palmityl, lauryl, myristyl and stearyl derivatives of ethylene diamine and the substituted ethylene diamines and retaining said compound in the materials.

13. Process for increasing the fastness of colorations produced with the aid of anthraquinone dyestuffs on materials comprising an organic derivative of cellulose, which comprises incorporating in the materials a compound selected from the group consisting of oleyl, palmityl, lauryl, myristyl and stearyl, derivatives of ethylene diamine and substituted ethylene diamines and retaining said compound in the materials.

14. Process for increasing the fastness of colorations produced with the aid of anthraquinone 150 dyestuITs on materials comprising cellulose acetate, which comprises incorporating in the materials a compound selected from the group consisting of the oleyl, palmityl, lauryl, myristyl and stearyl derivatives of ethylene diamine and substituted ethylene diamines and retaining said compound in the materials.

15. Process for increasing the fastness to light of colorations produced by dyes on materials comprising cellulose acetate, which comprises applying to the materials in the form of aqueous dispersions a compound selected from the group consisting of the amides and substituted amides of higher fatty acids and retaining said compound in the materials.

16. In a process for increasing the fastness to light of colorations produced by dyes on materials comprising filaments containing an organic derivative of cellulose, the step of incorporating in the solutions from which the filaments are spun a compound selected from the group consisting of the amides and substituted amides of higher fatty acids.

17. In a process for increasing the fastness to light of colorations produced by dyes on materials comprising filaments containing cellulose acetate, the step of incorporating in the solutions from which the filaments are spun a compound selected from the group consisting of the amides and substituted amides of higher fatty acids.

18. Materials comprising an organic derivative of cellulose colored with a dyestuff selected from the group consisting of the amino anthraquinone, alkylamino anthraquinone and substituted alkylamino anthraquinone dyestuffs and having incorporated therein a compound selected from the group consisting of the amides and substituted amides of organic carboxylic acids containing more than four carbon atoms.

19. Materials comprising cellulose acetate colored with a dyestufi selected from the group consisting of the amino anthraquinone, alkylamino anthraquinone and substituted alkylamino anthraquinone dyestuffs and having incorporated therein a compound selected from the group consisting of the amides and substituted amides of higher fatty acids.

20. Materials comprising an organic derivative of cellulose colored with a dyestuff selected from the group consisting of the amino anthraquinone, alkylamino anthraquinone and substituted alkylamino anthraquinone dyestuffs and having incorporated therein a compound selected from the group consisting of oleyl palmityl, lauryl, myristyl and stearyl derivatives of ethylene diamine and the substituted ethylene diamines.

21. Materials comprising cellulose acetate colored with a dyestuff selected from the group consisting of the amino anthraquinone, alkylamino anthraquinone and substituted alkylamino anthraquinone dyestufis and having incorporated therein a compound selected from the group consisting of oleyl palmityl, lauryl, myristyl and stearyl derivatives of ethylene diamine and the substituted ethylene diamines.

GEORGE HOLLAND ELLIS. HENRY CHARLES OLPIN. ERNEST WILLIAM KIRK. 

